Process for preparation of substituted aromatic compound

Abstract

A substituted aromatic compound substituted with Q is obtained by reacting a phosphazenium compound represented by formula (1) (in the formula, Q − represents an anion in a form derived by elimination of a proton from an inorganic acid, or an active hydrogen compound having an active hydrogen on an oxygen atom, a nitrogen atom or a sulfur atom; a, b, c and d, each independently, is 0 or 1, but all of them are not 0 simultaneously; and R groups represent the same or different hydrocarbon groups having 1 to 10 carbon atoms, or two Rs on each common nitrogen atom may be bonded together to form a ring structure) with a halogenated aromatic compound having halogen atoms; whereby, at least one halogen atom in the halogenated aromatic compound is substituted with Q (where, Q represents an inorganic group or an organic group in a form derived by elimination of one electron from Q − in formula (1)).

What is claimed is:  
     
       1. A process for preparation of a substituted aromatic compound substituted with Q, which comprises: 
       reacting a phosphazenium compound represented by formula (1)                    
        (in the formula,  
       Q −  represents an anion in a form derived by elimination of a proton from an inorganic acid, or an active hydrogen compound having an active hydrogen on an oxygen atom, a nitrogen atom or a sulfur atom;  
       a, b, c and d, each independently, is 0 or 1, but all of them are not 0 simultaneously; and  
       R groups represent the same or different hydrocarbon groups having 1 to 10 carbon atoms, or two Rs on each common nitrogen atom may be bonded together to form a ring structure) with a halogenated aromatic compound having halogen atoms;  
       whereby, at least one halogen atom in the halogenated aromatic compound is substituted with Q (where, Q represents an inorganic group or an organic group in a form derived by elimination of one electron from Q −  in formula (1)). 
     
     
       2. A process according to  claim 1 , wherein: 
       a phosphazenium compound represented by formula (2)                    
        (in the formula, Z −  is a halogen anion, and a, b, c, d and R groups are the same meaning as described above) and a metal compound represented by MQ n  (in the formula, M represents an alkaline metal atom, an alkaline earth metal atom, or a rare earth metal atom, Q is the same meaning as described above, and n is an integer from 1 to 3) are used as raw materials and made contact with each other to produce a phosphazenium compound represented by the formula (1) in the reaction system; whereby, at least one halogen atom in the halogenated aromatic compound is substituted with Q.  
     
     
       3. A process according to  claim 1 , wherein at least three of a, b, c and d are 1. 
     
     
       4. A process according to  claim 2 , wherein at least three of a, b, c and d are 1. 
     
     
       5. A process according to  claim 1 , wherein all of the R groups are the same or different aliphatic hydrocarbon groups having 1 to 10 carbon atoms. 
     
     
       6. A process according to  claim 2 , wherein all of the R groups are the same or different aliphatic hydrocarbon groups having 1 to 10 carbon atoms. 
     
     
       7. A process according to  claim 5 , wherein all of the R groups are a methyl group. 
     
     
       8. A process according to  claim 6 , wherein all of the R groups are a methyl group. 
     
     
       9. A process according to  claim 1 , wherein among at least part of the R groups, two R groups on the same nitrogen atom are bonded to each other to form a ring structure; the divalent substituent formed by the bond of the two R groups being tetramethylene or pentamethylene. 
     
     
       10. A process according to  claim 2 , wherein among at least part of the R groups, two R groups on the same nitrogen atom are bonded to each other to form a ring structure; the divalent substituent formed by the bond of the two R groups being tetramethylene or pentamethylene. 
     
     
       11. A process according to  claim 1 , wherein a compound from which Q −  in formula (1) is derived is one of hydrogen halides, hydrogen cyanide, thiocyanic acid, water, carboxylic acids having 1 to 20 carbon atoms, alcohols having 1 to 20 carbon atoms, aromatic compounds having 6 to 20 carbon atoms and 1 to 3 hydroxyl groups, aliphatic or aromatic secondary amines having 2 to 20 carbon atoms, monovalent thiols and aromatic mercapto compounds. 
     
     
       12. A process according to  claim 2 , wherein a compound from which Q −  in formula (1) and Q in MQ n  are derived is one of hydrogen halides, hydrogen cyanide, thiocyanic acid, water, carboxylic acids having 1 to 20 carbon atoms, alcohols having 1 to 20 carbon atoms, aromatic compounds having 6 to 20 carbon atoms and 1 to 3 hydroxyl groups, aliphatic or aromatic secondary amines having 2 to 20 carbon atoms, monovalent thiols and aromatic mercapto compounds. 
     
     
       13. A process according to  claim 1 , wherein when Q −  in formula (1) is not F − , the halogenated aromatic compound is inactive fluorinated aromatic hydrocarbon compound, inactive chlorinated aromatic hydrocarbon compound, inactive brominated aromatic hydrocarbon compound, active fluorinated aromatic hydrocarbon compound, active chlorinated aromatic hydrocarbon compound, active brominated aromatic hydrocarbon compound, chlorinated aromatic heterocyclic compound or brominated aromatic heterocyclic compound. 
     
     
       14. A process according to  claim 2 , wherein when Q −  in formula (1) and Q in MQ n  are not F −  and F, respectively, the halogenated aromatic compound is inactive fluorinated aromatic hydrocarbon compound, inactive chlorinated aromatic hydrocarbon compound, inactive brominated aromatic hydrocarbon compound, active fluorinated aromatic hydrocarbon compound, active chlorinated aromatic hydrocarbon compound, active brominated aromatic hydrocarbon compound, chlorinated aromatic heterocyclic compound or brominated aromatic heterocyclic compound. 
     
     
       15. A process according to  claim 1 , wherein when Q −  in formula (1) is F − , the halogenated aromatic compound is inactive chlorinated aromatic hydrocarbon compound, inactive brominated aromatic hydrocarbon compound, active chlorinated aromatic hydrocarbon compound, active brominated aromatic hydrocarbon compound, chlorinated aromatic heterocyclic compound or brominated aromatic heterocyclic compound. 
     
     
       16. A process according to  claim 2 , wherein when Q −  in formula (1) and Q in MQ n  are F −  and F, respectively, the halogenated aromatic compound is inactive chlorinated aromatic hydrocarbon compound, inactive brominated aromatic hydrocarbon compound, active chlorinated aromatic hydrocarbon compound, active brominated aromatic hydrocarbon compound, chlorinated aromatic heterocyclic compound or brominated aromatic heterocyclic compound. 
     
     
       17. A process according to  claim 2 , wherein M in MQ n  is an alkaline metal atom.